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Applications of dihydroarenediols to chemoenzymatic synthesis : approaches to total synthesis of morphine alkaloids

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dc.contributor.author Finn, Kevin J. en_US
dc.date.accessioned 2009-05-28T16:39:38Z
dc.date.available 2009-05-28T16:39:38Z
dc.date.issued 2006-05-28T16:39:38Z
dc.identifier.uri http://hdl.handle.net/10464/1453
dc.description.abstract The present studies describe, as a primary goal, our recent progess toward the synthesis of morphine alkaloids from aromatic precursors. Model substrates were synthesized which allowed investigation into Diels-Alder, radical cascade, and palladium-catalyzed bond-forming reactions as possible routes to the morphine alkaloid skeleton. As a secondary objective, three separate series of aromatic substrates were subjected to whole-cell oxidation with Escherichia coli JM 109 (pDTG601), a recombinant organism over-expressing the enzyme toluene dioxygenase. Included in this study were bromothioanisoles, dibromobenzenes, and cyclopropylbenzene derivatives. The products of oxidation were characterized by chemical conversion to known intermediates. The synthetic utility of one of these bacterial metabolites, derived from oxidation of o-dibromobenezene, was demonstrated by chemical conversion to (-)conduritol E. en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Morphine--Synthesis. en_US
dc.subject Aromatic compounds--Oxidation. en_US
dc.title Applications of dihydroarenediols to chemoenzymatic synthesis : approaches to total synthesis of morphine alkaloids en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name Ph.D. Chemistry en_US
dc.degree.level Doctoral en_US
dc.contributor.department Department of Chemistry en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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